X-ray crystal and computational structural study of (E)-2-[(2-chloro­phenyl)­iminometh­yl]-4-methoxy­phenol

Özek, A.; Büyükgüngör, O.; Albayrak, Ç.; Odabaşoğlu, M.

doi:10.1107/S1600536808021958

Volume 64
Part 8
Pages o1579-o1580
August 2008

Received 11 July 2008
Accepted 14 July 2008
Online 23 July 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.031
wR = 0.090
Data-to-parameter ratio = 14.6
Details

X-ray crystal and computational structural study of (E)-2-[(2-chlorophenyl)iminomethyl]-4-methoxyphenol

Arzu Özek,^a ^* Orhan Büyükgüngör,^a Çigdem Albayrak ^b and Mustafa Odabasoglu ^b

^aDepartment of Physics, Ondokuz Mayis University, TR-55139 Samsun, Turkey, and ^bDepartment of Chemistry, Ondokuz Mayis University, TR-55139 Samsun, Turkey
Correspondence e-mail: arzuozek@omu.edu.tr

In the molecule of the title compound, C₁₄H₁₂ClNO, the two aromatic rings are oriented at a dihedral angle of 12.28 (7)°. An intramolecular O-HN hydrogen bond results in the formation of a nearly planar six-membered ring, which is oriented with respect to the aromatic rings at dihedral angles of 0.18 (5) and 12.10 (6)°. In the crystal structure, weak intermolecular C-HO hydrogen bonds link the molecules into chains along the c axis. There is a C-H [pi] contact between the methyl group and the chlorophenyl ring and a [pi] - [pi] contact between the two benzene rings [centroid-centroid distance = 3.866 (1) Å].

Related literature

For related literature, see: Özek et al. (2007); Odabasoglu, Büyükgüngör et al. (2007); Odabasoglu, Arslan et al. (2007); Albayrak et al. (2005); Elerman et al. (1995); Frisch et al. (2004). For general background, see: Friesner (2005); Liu et al. (2004).

Experimental

Crystal data

C₁₄H₁₂ClNO₂
M_r = 261.70
Monoclinic, P 2₁ /c
a = 13.2348 (9) Å
b = 8.4701 (4) Å
c = 12.0115 (8) Å
= 112.846 (5)°
V = 1240.86 (13) Å³
Z = 4
Mo K radiation
= 0.30 mm^-1
T = 296 K
0.56 × 0.40 × 0.11 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.851, T_max = 0.966
15517 measured reflections
2441 independent reflections
1977 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.089
S = 1.05
2441 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.13 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C9-C14 ring.

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.80 (2)	1.85 (2)	2.5896 (16)	152 (2)
C8-H8O1ⁱ	0.93	2.58	3.4960 (19)	169
C7-H7bCg2ⁱⁱ	0.96	2.90	3.682	139
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Table 2
Selected geometric parameters (Å, °) calculated with X-ray, AM1, PM3, HF and DFT

Parameters	X-ray	AM1	PM3	HF^a	DFT/B3LYP^a
C8-N1	1.278 (17)	1.292	1.302	1.262	1.294
C2-O1	1.357 (17)	1.366	1.355	1.332	1.341
C1-C6	1.407 (18)	1.412	1.406	1.408	1.416
C1-C8	1.447 (19)	1.465	1.478	1.463	1.446
C1-C2	1.399 (19)	1.404	1.408	1.392	1.418
N1-C9	1.408 (17)	1.408	1.427	1.402	1.399
C9-C10	1.392 (18)	1.417	1.402	1.393	1.409
C10-Cl1	1.734 (14)	1.699	1.680	1.741	1.755
C5-O2	1.369 (17)	1.385	1.385	1.354	1.369

C9-C10-Cl1	120.02 (10)	120.869	120.554	120.163	119.783
C6-C5-O2	125.3 (15)	124.874	125.684	125.547	125.410
C6-C1-C8	119.24 (13)	116.155	117.987	117.891	119.224
C9-N1-C8	122.41 (12)	121.909	122.720	120.140	121.089
C14-C9-N1	124.73 (12)	123.114	123.424	122.078	122.787
N1-C8-C1	120.75 (13)	123.585	119.187	123.458	122.291
N1-C9-C10	117.64 (12)	118.844	116.913	119.874	119.562

C8-C1-C2-O1	0.6 (2)	-0.034	0.012	-0.194	-0.175
C6-C5-O2-C7	-1.7 (2)	0.543	-0.485	0.568	0.096
C10-C9-N1-C8	-165.93 (12)	-147.255	-179.982	-134.578	-144.790
N1-C8-C1-C6	176.91 (12)	176.946	-179.997	179.409	179.781
C1-C8-N1-C9	-178.32 (11)	-179.082	179.999	-178.064	-176.682
Note: (a) 6-31G(d,p).

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2494 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant No. F.279 of the University Research Fund).

References

Albayrak, Ç., Odabasoglu, M. & Büyükgüngör, O. (2005). Acta Cryst. E61, o423-o424.
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Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Friesner, R. A. (2005). Proc. Natl Acad. Sci. USA, 102, 6648.
Frisch, M. J. et al. (2004). GAUSSIAN03. Revision E.01. Gaussian Inc., Wallingford, CT 06492, USA.
Liu, H., Bandeira, N. A. G., Calhorda, M. J., Drew, M. G. B., Felix, V., Novosad, J., De Biani, F. F. & Zanello, P. (2004). J. Organomet. Chem. 689, 2808-2819.
Odabasoglu, M., Arslan, F., Ölmez, H. & Büyükgüngör, O. (2007). Acta Cryst. E63, o3654.
Odabasoglu, M., Büyükgüngör, O., Narayana, B., Vijesh, A. M. & Yathirajan, H. S. (2007). Acta Cryst. E63, o1916-o1918.
Özek, A., Albayrak, Ç., Odabasoglu, M. & Büyükgüngör, O. (2007). Acta Cryst. C63, o177-o180.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.

organic compounds